We look back at 12 years of iTunes releases.

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We're still waiting for the newest version of iTunes, which Apple introduced in September during its iPhone 5 media event. The makeover, which will undoubtedly end up as version 11.0 (though Apple isn't publicly referring to it as such), consists of a "dramatically simplified new interface," better iCloud integration, a revamped mini-player, and Facebook integration.

iTunes has walked a long road to reach this point—version 1.0 appeared in January 2001. While we're waiting for Apple's new ship date of "late November" to arrive, let's take a look back at how iTunes has evolved in the last 12 years.

iTunes 1.0: "World’s Best and Easiest To Use Jukebox Software"

As mentioned above, iTunes was first released in January 2001. Apple advertised it as the most amazing jukebox software the world has ever seen, allowing users to rip CDs into MP3s and organize their music within an easy-to-use interface. The tagline "Rip. Mix. Burn." essentially came from this release—Apple emphasized the ability of users to make their own CD mixes and re-burn them back to CD, like a mix tape. At the time of this release, the iPod had not yet made its public debut—that came later in the year. So those MP3s you were ripping? They were meant to be synced to some other MP3 player, such as those that were available from Creative Labs or Rio. A week after the original release of iTunes, Apple announced it had seen a whopping 275,000 downloads from Mac users.

iTunes 2.0: Enter the iPod

The second full-point release of iTunes came 10 months after the first. That was because Apple finally revealed its ultra-secret project: the iPod. Apple advertised this release of iTunes as having "seamless integration" with its new MP3 player, with songs and playlists automatically syncing to the iPod over FireWire. Apple also added an equalizer and cross fading with this release, and began bundling iTunes with OS X. The software also allowed users to burn CDs of MP3 files, not just traditional CDs, so people could store more music than ever on their iTunes-mixed CDs.

iTunes 3.0: Smart playlists debut

iTunes 3 was released in July 2002. The headline feature was smart playlists, which allowed users to create dynamic playlists based on a set of rules (like mail rules). If you wanted a playlist of your 20 most listened-to songs, or only songs you added since a certain date, iTunes would be happy to do it for you. iTunes 3 also came with "Sound Check," Apple's system for adjusting the volume of your playlist to a consistent level, and support for audiobooks from Audible.com.

iTunes 4.0: Music store, here we come

iTunes 4 was released in April 2003, bringing with it the first version of the iTunes Music Store. This, you can imagine, was huge—at the time, most Internet users were still either buying music in CD form or just pirating away. Buying music from a major company like Apple was something of a foreign concept, but Apple wooed users by offering individual songs for 99¢ apiece—now, everything was a single that you could cherry pick. Along with the iTunes Store came Apple's proprietary FairPlay DRM; users could burn music to an unlimited number of CDs or sync to an unlimited number of iPods, but only three Macs could play the files. FairPlay ended up being in place on music sold through the iTunes Store until 2009, when Apple introduced DRM-free "iTunes Plus" tracks.

iTunes 5.0: iPod nano, podcasts, and more

With iTunes 5, Apple moved major point releases of the app to the fall. The iPod nano had just been announced at the same 2005 media event, and iTunes 5 was (naturally) built to support it. Apple also added features like Smart Shuffle (Apple's attempt at making its random feature more, well, random), and allowed Windows users to sync their Outlook contacts and calendars to their iPods. (Just prior to the 5.0 release, Apple had released its first version of iTunes for Windows.) Leading up to this release, Apple had added podcast support to the software, as well as support for video, and "AirTunes" (what eventually became AirPlay), and support for the Motorola ROKR E1—arguably the "first" iPhone to hit the market before Apple released its own a couple years later. The phone was the first to fully integrate with iTunes, though Apple was reportedly never thrilled with Motorola's offering.

iTunes 6.0: Music videos galore

iTunes 6 arrived only a month after the release of iTunes 5—Apple was pretty loose with its full version numbers back then. In October of 2005, Apple added music videos to the iTunes Store for the first time, as well as a small handful of TV shows like Desperate Housewives, Lost, and Night Stalker for $1.99 per episode. This was TV's first foray into iTunes and the networks were wary of being taken advantage of by Apple. iTunes Store users could also purchase short films from Pixar for $1.99, foreshadowing the eventual release of movies through iTunes.

iTunes 7.0: Movies, movies, movies!

In September 2006, Apple introduced iTunes 7 as the "most significant enhancement to the world’s most popular music jukebox and online music and video store." Indeed, this was the release where Cover Flow made its first appearance, and the iTunes Store began carrying a whopping 75 movies from studios like Disney, Pixar, Touchstone, and Miramax. The films could be synced with users' iPods for on-the-go viewing, or could be played via Apple's soon-to-be-released Apple TV (then nicknamed "iTV" by Apple). Between the release of iTunes 6 and 7, Apple had made the software into a universal binary so it could be run on both Intel and PowerPC Macs, and added support for Nike+iPod—Apple's fitness collaboration with Nike. iTunes 7 was also the first version of iTunes that allowed users to sync iTunes-purchased music backfrom their iPods onto an authorized computer.

iTunes 8.0: Genius time

Genius playlists became a thing with this release.

iTunes 8 was released in September 2008, two full years after iTunes 7. The major new feature was Genius playlists—Apple's algorithm for generating playlists based on a single song, where the selected songs were supposed to "go great together." Then there was the Genius Sidebar, an opt-in service that sent your iTunes library data back to the iTunes Store so Apple could eventually refine exactly which songs went so great together. But that wasn't all. Apple had also begun adding HD TV shows to the iTunes Store, and previously, it had added support for iPhone activation (the iPhone was released a year and some months prior). You could also download your movie or TV purchases that you made from an Apple TV to your computer as well, allowing users to make a backup of the media they'd bought elsewhere.

iTunes 9.0: Sharing is caring

iTunes-Store-exclusive features, such as iTunes LP and iTunes Extras, became big with the release of iTunes 9 in September of 2009. Apple also added Genius Mixes along with a new Home Sharing feature, which allowed different iTunes account holders on the same network to see and share each other's DRM-free music through iTunes. Previously, users had to send around files to their loved ones; this was the first time Apple added file sharing capabilities directly into iTunes. Leading up to iTunes 9, Apple added support for the rental of HD movies, replaced Party Shuffle with iTunes DJ as a way for users to queue up music in a party environment, and stopped syncing with the Palm Pre. Also, with the release of iTunes 9, Apple made it possible for users to organize their iPhone apps directly from within iTunes, which would then be reflected on their iPhones without any extra steps. Hallelujah!

iTunes 10: The Ping that gets no response

Enlarge/ Apple's social network Ping made its debut in 2010, but it didn't last long.

Apple

Apple's first attempt at integrating iTunes into a social network came in September of 2010. Dubbed "Ping," the network was meant as a sort of Facebook-mashed-with-iTunes offering that let users share what they were buying or listening to with friends. Users could also follow artist pages to get firsthand info from their favorite musicians, such as concert dates or other musings. With the release of iTunes 10, AirTunes officially became AirPlay, which Apple now uses to allow Macs and iOS devices to stream audio and video to AirPlay-compatible gadgets. iTunes Match also made its debut with this release, letting users who had ripped (or *cough* pirated) MP3s pay a fee to "match" that music with songs on the iTunes Store. iTunes Match users could then download and play that music on a plethora of iOS devices, though some users feared Apple would keep track of the iTunes Match data and report music pirates to the authorities.

iTunes 11: A fresh start

Well, we know about the next major version of iTunes because Apple gave us a preview in September of 2012. But the company pushed its original release date of "late October" to "late November," so at this point, all we have to work with is what Apple has presented us.

The newest version of iTunes will have a more album-focused interface.

Nathan Mattise

So what makes the next version of iTunes so great? For one, it has a revamped UI meant to provide a more themed experience when listening to albums. It also has better integration with iCloud, which now automatically downloads your iOS device purchases directly to your iTunes library on the computer. And finally, iTunes can pick up on a movie where you left off on your iPhone or iPad. Oh, and did we mention the redesigned Mini Player?

The redesigned Mini Player.

Nathan Mattise

Apple has decided to shut down Ping and move onto greener pastures. Instead, the iTunes Store itself will be able to offer some Ping-like features, such as artist pages with information about shows. And similarly, purchases can still be "liked," but they'll be posted to Twitter and/or Facebook instead of Apple's own offering.

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Jacqui Cheng
Jacqui is an Editor at Large at Ars Technica, where she has spent the last eight years writing about Apple culture, gadgets, social networking, privacy, and more. Emailjacqui@arstechnica.com//Twitter@eJacqui

The "browse" view was perhaps the single most important feature of iTunes. It seems obvious now, but back then managing music was a pain and the solution had always been based on file management and a separate window for each playlist. Music players typically had a billion different windows, one for nearly every feature. We didn't realize how maddening those programs were until iTunes came on the scene. Yes maddening. Remember how all those little windows snapped together as if that was the path to simplicity?

Way back when (7-8 yrs ago ?), I had painstakingly ripped my 1,000+ CDs to FLAC, and contemplated getting into iPhones/iPods, only to discover that:1- iTunes didn't handle FLAC2- iTunes choked on such a large collectionI'm not sure what the situation on both accounts is now. But it sure turned me off lock-in and proprietary setups. My Android doodads let me just cut and paste music and playlists from Windows Explorer, and I just finished a several-days-long upload off all of it to Google Music, so it should be available from the cloud, in a pinch.

Way back when (7-8 yrs ago ?), I had painstakingly ripped my 1,000+ CDs to FLAC, and contemplated getting into iPhones/iPods, only to discover that:1- iTunes didn't handle FLAC

This may help with playing FLAC/OGG in iTunes. I haven't tried it particularly recently, but it worked fine the last time I did.

obarthelemy wrote:

2- iTunes choked on such a large collection

I've got 591 albums (totalling 825 discs) and searching has always (since iTunes 10, at least) been instantaneous, and scrolling is extremely smooth on any Mac I've tried. I've not tried iTunes on Windows with a big library for a while, but I believe it's not as good.

obarthelemy wrote:

But it sure turned me off lock-in and proprietary setups.

On a Mac, Windows Phone can sync with iTunes just fine, through a free app.

As I looked at this, iTunes is like iOS, 10 versions with almost no change to the UI, same dull grey, same 3 control buttons on top left. A few more options here and there, but basically the same... quite boring UI at best.

I rarely use it for anything other than syncing my iPad/iPhone; many of its features I find to be lacking in simplicity and even those are geared toward marketing stuff that I have no interest in. It's not really very user friendly, and its customization is sorely lacking. It's lack of support for many audio codecs is pretty appalling as well.

The few items I've bought through iTunes only get looked at through the interface long enough to transfer to a much better media player (imo of course). The software itself is bloated, and I find Apple's secrecy with what is included in the iTunes installer to be underhanded and sneaky especially since much of it seems to be unnecessary for most tasks.

I like Apple products, they're useful and work passably, however iTunes is not, nor has ever been, one of them.

The article seems to have left out a mention of the incredibly crappy CD driver filters that iTunes installs in Windows that are the cause of more blue screens and other issues than any other single app I've come in contact with. That one facet of iTunes is what keeps it off all machines I manage.

With each new release of iTunes, we aficionados of classical music look to see if it has finally incorporated features appropriate for that genre. We are always dissappointed.

One desirable feature would be the simple recognition that one track on a CD and one complete musical work are not synonymous; a single classical work often occupies several tracks and sometimes more than one disc. It would be nice to have the list of works have a little reveal triangle next to the name of a work; clicking it would display the individual movements or sections of the work.

Also nice would be an interface to the internal database that includes fields for the wide range of information normally associated with a classical music performance or recording.

As I looked at this, iTunes is like iOS, 10 versions with almost no change to the UI, same dull grey, same 3 control buttons on top left. A few more options here and there, but basically the same... quite boring UI at best.

Just like how the PlayStation controller is the same boring layout too. I wish companies would change things for the sake of change and be just as intuitive as Windows 8 or TouchWiz.

Seriously. >1 minute from clicking the icon to the actual application being there. It happens to me that I'm browsing the 'net and I've actually forgotten that iTunes is still starting, and all of a sudden it appears over the browser window. On a 3 year old quad-core PC, not new by any stretch but plenty fast for anything at home except iTunes. Winamp / songbird take a few seconds to start at most.

iTunes needs some serious work under the hood. I hadn't used it for years until I bought an iPad and was locked in again.

Really weird to see how few things have actually changed. Pretty ingenious base design actually, one view with different columns for artist, title etc. and a search window that lets you search immediately. Add playlists and all the other stuff is just fluff. People seem to love to hate it but I actually think its really good. Definitely much nicer than Winamp was (see picture above) It is fast on my Mac (which is the single problem it has on Windows) and apart from that it does everything you would want from a music library software. Single problem I have is that I moved to the Android world so I loose the great syncing capabilities. You never appreciate things until you loose them.

For most things the online cloud integration of Android is much better than anything Apple could provide but when it comes to Media libraries I truly miss the Apple ecosystem.

(It sucks for movies though, that is the one thing Apple doesn't seem to get, all the competitors offer much better media support, and unlike music where transcoding a file takes 3 seconds, using handbrake on movies is annoying. Much better to simply install VLC and remove all Apple media players from the open actions of files)

It's has some neat features, but the performance is terrible, and the UI is a nightmare. Worse than that, the way it handles things is unintuitive. Almost everyone with an "i device" (iPad, iPod, iPhone) HATES dealing with iTunes, because it does unexpected things.

The issue, of course, is the concept of "syncing". iTunes forces you do "sync" in order to do ANYTHING. It sounds nice, and is conceptually simple, but in practice, it's confusing for most people. Most people just want to copy THIS file to THAT location. iTunes, and in fact the entire Apple device "ecosystem", doesn't really let you do that. YOU MUST SYNC.

But Apple doesn't change it, because they never listen to their customers. The Apple Way is, by definition, perfect. You don't like it? Then you need to change. What blows me away is that so many Apple users defend Apple's "screw the desires of our customers" attitude.

Prior to the music store being release, the killer feature for every college student was the ability to access and stream everyone else's library who was on the same subnet as you. With Sharetunes, users could actually download those tracks and seamlessly add it to their own library. This was basically a short-lived Napster of the early 2000's before Apple had to start sucking up to record companies, broke sharetunes, and limited the number of computers that could connect on the same subnet to 5.

It's has some neat features, but the performance is terrible, and the UI is a nightmare. Worse than that, the way it handles things is unintuitive. Almost everyone with an "i device" (iPad, iPod, iPhone) HATES dealing with iTunes, because it does unexpected things.

The issue, of course, is the concept of "syncing". iTunes forces you do "sync" in order to do ANYTHING. It sounds nice, and is conceptually simple, but in practice, it's confusing for most people. Most people just want to copy THIS file to THAT location. iTunes, and in fact the entire Apple device "ecosystem", doesn't really let you do that. YOU MUST SYNC.

But Apple doesn't change it, because they never listen to their customers. The Apple Way is, by definition, perfect. You don't like it? Then you need to change. What blows me away is that so many Apple users defend Apple's "screw the desires of our customers" attitude.

Been using iTunes since 1.0, and iPod since launch, and iPhone since launch, and iPad since launch......And I love everything about iTunes except the occasional "No, you can't put that version of iOS on that device that previously ran it, WHAT ARE YOU THINKING?"

And why, on a device that takes care of such mundane shit for me, would I give a flying fuck exactly where the file goes? I don't, so long as it's usable, and it has been since iTunes 2 with the very first iPod.

Apple doesn't listen to their customers? You must have missed that Tim Cook recently defiled the grave of Jobs by releasing a smaller iPad. They sure as fuck didn't do it because they wanted to. Jobs made absolutely no bones about how stupid an idea he thought smaller tablets was, but here we are, with nit-picky bastards like you forcing them to make inane, market-following shit. Thanks for that, by the way.

iTunes was allowed because of the small user base. It was Mac-only for a long time, labels wanted to see what Apple could do with it. Now they kind of regret it...but they shouldn't. Same for video, get your poop in a pile and commit to something fair and reasonable.

I think music and video content should be like radio, you pay a royalty for content that anyone can use. Government mandated negotiations that negotiate broad use. This would foster innovation like crazy, instead of the stagnated magacorp'opolies that we have now.

iTunes sucks.The issue, of course, is the concept of "syncing". iTunes forces you do "sync" in order to do ANYTHING. It sounds nice, and is conceptually simple, but in practice, it's confusing for most people. Most people just want to copy THIS file to THAT location. iTunes, and in fact the entire Apple device "ecosystem", doesn't really let you do that. YOU MUST SYNC.

Really weird to see how few things have actually changed. Pretty ingenious base design actually

You're actually the first person I've ever seen describing itunes as "ingenious". I was about to fall off my chair when I read it, because seriously, itunes is such a stinky turd that there's no word in any language to describe it properly. The app itself is monstrously bloated and slow, and the user interface is horrific. Updating apps on my iphone requires an inordinate amount of clicks, the whole process is thoroughly unintuitive, apps don't synch automatically over to the phone and buttons and features are hidden away in corners and other odd places where they are easily missed and don't make sense. Seriously, a blind person could have designed a better looking and smoother functioning graphical user interface.

No, itunes is an atrocious monstrosity, and whomever is behind it should be dragged out back and given an extremely firm punting to their rear end(s)...

Way back when (7-8 yrs ago ?), I had painstakingly ripped my 1,000+ CDs to FLAC, and contemplated getting into iPhones/iPods, only to discover that:1- iTunes didn't handle FLAC2- iTunes choked on such a large collectionI'm not sure what the situation on both accounts is now. But it sure turned me off lock-in and proprietary setups. My Android doodads let me just cut and paste music and playlists from Windows Explorer, and I just finished a several-days-long upload off all of it to Google Music, so it should be available from the cloud, in a pinch.

iTunes lack of FLAC support: Agreed; although it's not used by many so I see why they don't worry about it, but I wouldn't think it's a big deal to add one codec...

Choking on a library of 400GB of music (conservative estimate: 1000 CDs * 10 tracks/CD * 40MB/track) for the collection you mention I don't think it was just iTunes that would have some hiccups on that when you are looking at computers from 7-8 years ago!

But for FLAC in the cloud, do you often find yourself in a high end listening environment and need to download some music? No phones/mp3 players can play at some high quality, and if they did, do you carry around $300+ headphones? Without a lot of money into your car stereo that's not a great listening environment; and even then it'd only be when you are parked - road noise would kill it otherwise.

I'm thankful for iTunes because in the distant past when I vaguely considered getting an iDevice I was always partly put off by knowing I'd have to use the monstrosity that was iTunes on Windows. Ever since it was forced on me when I installed Quicktime I quickly realized that with Apple devices you either went all in or would have an even more subpar experience than their usual.

I know much of this is no longer the case but I'm thankful for iTunes helping to prevent me making an expensive mistake and buying products not suited to my needs.

It's has some neat features, but the performance is terrible, and the UI is a nightmare. Worse than that, the way it handles things is unintuitive. Almost everyone with an "i device" (iPad, iPod, iPhone) HATES dealing with iTunes, because it does unexpected things.

The issue, of course, is the concept of "syncing". iTunes forces you do "sync" in order to do ANYTHING. It sounds nice, and is conceptually simple, but in practice, it's confusing for most people. Most people just want to copy THIS file to THAT location. iTunes, and in fact the entire Apple device "ecosystem", doesn't really let you do that. YOU MUST SYNC.

But Apple doesn't change it, because they never listen to their customers. The Apple Way is, by definition, perfect. You don't like it? Then you need to change. What blows me away is that so many Apple users defend Apple's "screw the desires of our customers" attitude.

MOST people don't want to think about their files. You may, because you are interested in technology, but most people don't care at all. And that's why iTunes works great for everyone. For the MOST people it just does it for you. For people that like technology enough to read Ars we can also figure out how to move this file to that location with whatever tool we like.

And for all the people who need to yell "iTunes sucks", what do you use? What works better with similar functionality? I have never found anything that I like enough to keep me from moving back to iTunes.

I used to love WinAmp, and it's still fast, but it lacks the vast amount of functionality and integration iTunes offers. Songbird? I thought that was a great idea, but after trying it several times I always come back to iTunes when Songbird is missing a feature I need or has some hiccup (although I haven't tried it in close to a year now).

It's has some neat features, but the performance is terrible, and the UI is a nightmare. Worse than that, the way it handles things is unintuitive. Almost everyone with an "i device" (iPad, iPod, iPhone) HATES dealing with iTunes, because it does unexpected things.

The issue, of course, is the concept of "syncing". iTunes forces you do "sync" in order to do ANYTHING. It sounds nice, and is conceptually simple, but in practice, it's confusing for most people. Most people just want to copy THIS file to THAT location. iTunes, and in fact the entire Apple device "ecosystem", doesn't really let you do that. YOU MUST SYNC.

But Apple doesn't change it, because they never listen to their customers. The Apple Way is, by definition, perfect. You don't like it? Then you need to change. What blows me away is that so many Apple users defend Apple's "screw the desires of our customers" attitude.

MOST people don't want to think about their files. You may, because you are interested in technology, but most people don't care at all. And that's why iTunes works great for everyone. For the MOST people it just does it for you. For people that like technology enough to read Ars we can also figure out how to move this file to that location with whatever tool we like.

And for all the people who need to yell "iTunes sucks", what do you use? What works better with similar functionality? I have never found anything that I like enough to keep me from moving back to iTunes.

I used to love WinAmp, and it's still fast, but it lacks the vast amount of functionality and integration iTunes offers. Songbird? I thought that was a great idea, but after trying it several times I always come back to iTunes when Songbird is missing a feature I need or has some hiccup (although I haven't tried it in close to a year now).

I use Winamp. Much better for my needs and since I don't own an iDevice there aren't any real issues with syncing although I believe it should sync with them too.

As I looked at this, iTunes is like iOS, 10 versions with almost no change to the UI, same dull grey, same 3 control buttons on top left. A few more options here and there, but basically the same... quite boring UI at best.

A user interface is *supposed* to be boring!Because it's the content that's important and the interface should not draw attention away from the important stuff.Also, consistency is very important. You (well, most people anyway) don't want to relearn a user interface after every other update.

I loved SoundJam MP. I loved it so much that I actively hated iTunes. I felt that Apple had bought and then killed the best music player, replacing it with a crappy copy. It took a couple of full number releases of iTunes before that hate went away. SoundJam was the basis for iTunes, yes, but iTunes always felt inferior.

As I looked at this, iTunes is like iOS, 10 versions with almost no change to the UI, same dull grey, same 3 control buttons on top left. A few more options here and there, but basically the same... quite boring UI at best.

A user interface is *supposed* to be boring!Because it's the content that's important and the interface should not draw attention away from the important stuff.Also, consistency is very important. You (well, most people anyway) don't want to relearn a user interface after every other update.

When a UI is so clunky and slow and gets in the way then you absolutely should change it. I think one of the flaws is that Apple treat it as a way to force their latest store on you rather than being a simple music App. I also don't like this trend in MS and Amazon products - I hate the way Apple's success has led to other companies compromising their software in an effort to emulate them.

Way back when (7-8 yrs ago ?), I had painstakingly ripped my 1,000+ CDs to FLAC, and contemplated getting into iPhones/iPods, only to discover that:1- iTunes didn't handle FLAC

This may help with playing FLAC/OGG in iTunes. I haven't tried it particularly recently, but it worked fine the last time I did.

obarthelemy wrote:

2- iTunes choked on such a large collection

I've got 591 albums (totalling 825 discs) and searching has always (since iTunes 10, at least) been instantaneous, and scrolling is extremely smooth on any Mac I've tried. I've not tried iTunes on Windows with a big library for a while, but I believe it's not as good.

obarthelemy wrote:

But it sure turned me off lock-in and proprietary setups.

On a Mac, Windows Phone can sync with iTunes just fine, through a free app.

I have a much, much larger collection and while iTunes does have too much bloat, I have never had any problem with speed when searching or scrolling. Even with my (sometimes) way too large album art. The only time I notice any real slow down is when the external drive I use to hold the files goes to sleep and has to spin up again. That, of course, is my own fault, but there is no way I am using my MBP's internal drive to hold all those files.

The issue, of course, is the concept of "syncing". iTunes forces you do "sync" in order to do ANYTHING. It sounds nice, and is conceptually simple, but in practice, it's confusing for most people. Most people just want to copy THIS file to THAT location. iTunes, and in fact the entire Apple device "ecosystem", doesn't really let you do that. YOU MUST SYNC.

Syncing _was_ great, in the beginning. With the iPod, MP3 players were huge and transfer speeds were quick with Firewire. (Yes, I know the iPod wasn't the first high capacity MP3 player, but when it was launched the majority of competitors still had 64MB flash.) Apple offered something where you kept your music on your own computer (this is before people had more than one computer), and whenever you plugged your iPod in, it'd make sure the same music was on it! That was a huge time-saver.

Things have changed. My iPhone can get music directly from the music store on the phone. I also don't have room for all my music, so I don't want to just throw everything on there. Some of it I prefer to stream from the cloud. And now we have apps — syncing was never a good idea for them. Why would I want the apps to be on my computer? I can't run them on there. And apps don't work like music, you don't usually want to transfer them all to one place at a time.

I hope the next iTunes makes some progress towards removing sync-pain. But I'm not holding my breath.

Every time it updates, the windows taskbar icon stops working. I have to make a new shortcut and drag it down. This started when version 10 came out.

I display my music in albums, 4 to a row, 4 rows visible. This is the only way that iTunes will scroll through the albums without skipping whole rows of music.

My music library is roughly 500GB, and iTunes hates it.

iTunes hates saving music to the hard drive that's entirely dedicated to my music collection. It once insisted on saving all music to its own folder on my system drive. I eventually broke it of that, but for about 5 releases, it would revert back after each update.

Finally, it doesn't play well with imported music. I got a lot of my music from roommates, people I lived with in the dorms, or...otherwise. Other music players pull in the relevant file information just fine, but iTunes labels nearly everything as "unknown album" with a date. Imagine trying to sort out dozens of GB worth of unknown albums by hand, because iTunes can't pull the file information from the internet.

It's has some neat features, but the performance is terrible, and the UI is a nightmare. Worse than that, the way it handles things is unintuitive. Almost everyone with an "i device" (iPad, iPod, iPhone) HATES dealing with iTunes, because it does unexpected things.

The issue, of course, is the concept of "syncing". iTunes forces you do "sync" in order to do ANYTHING. It sounds nice, and is conceptually simple, but in practice, it's confusing for most people. Most people just want to copy THIS file to THAT location. iTunes, and in fact the entire Apple device "ecosystem", doesn't really let you do that. YOU MUST SYNC.

But Apple doesn't change it, because they never listen to their customers. The Apple Way is, by definition, perfect. You don't like it? Then you need to change. What blows me away is that so many Apple users defend Apple's "screw the desires of our customers" attitude.

I am not sure what kind of a computer you have and I totally agree that iTunes on Windows is a pig. But on the Mac I wouldn't know what you are talking about. Sure its a bit heavy if you just want to play a single song but it starts in 2 seconds and my 50GB library scrolls, searches etc. instantanious without any slowdown, lag whatsoever. Not sure what kind of performance problems people have. (again not talking about windows that version works but is definitely not smooth in any form or shape)

And regarding syncing? Yeah Apple forces you to sync. But you know what its an AWESOME way to get your media to your mobile devices. The best possible way. If someone doesn't understand it, he should perhaps spend 5 minutes to learn it. Go to the sync section, music tab, select the playlists you want on your phone ... Done. I am not sure what is hard to understand about that.

The problem is you cannot really have both, you need to either sync or put files there manually, otherwise you get a terrible mix-up. The one problem for the Apple approach is if you do not want to use iTunes, for me that is for movies and I can see the argument for picture libraries as well, because not everybody wants to use iPhoto. In those cases the closed approach sucks. And taking away the file system may be good for a lot of base usecases but its terrible the moment you want to do something more complex. Like using multiple apps working with the same files. Android is much better here.

But for syncing music, podcasts etc.? I just switched to an Android device and I terribly miss the syncing ability. Dragging and dropping media files with the stupid Android File Transfer app that does not really work is torture. If you added a couple new files into the folder you only have the option to skip a single file or overwrite all? Who designed that kind of bullshit? You cannot queue multiple copy tasks as well and if you want your playlist its export playlist and copy as well, seriously I would sooner stick a needle in my eye. And given my internet connection limits (and my phsychological I want my files on my computer issues) the cloud stuff is not really an option.

So yeah iTunes may have its problems but itunes music syncing >>>>>>>>>> Android